


Painted By Numbers

by Cerberusia



Series: No-One Sleeps When I'm Awake [2]
Category: Teen Wolf (TV)
Genre: F/M, Femdom, Genderplay, Masturbation, Obedience, cross-dressing
Language: English
Status: Completed
Published: 2012-09-27
Updated: 2012-09-27
Packaged: 2017-11-15 04:01:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,809
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/522915
Author URL: https://archiveofourown.org/users/Cerberusia/pseuds/Cerberusia
Summary: <blockquote class="userstuff">
              <p>Of course, he does it for Lydia.</p><p>She doesn't tell him what she's measuring him for and he knows better than to ask, but when he turns up to their next session to find a bag waiting on her bed, he knows what he's meant to do.</p>
            </blockquote>





	Painted By Numbers

**Author's Note:**

> For my _crossdressing_ square for Kink Bingo.

Of course, he does it for Lydia.

She doesn't tell him what she's measuring him for and he knows better than to ask, but when he turns up to their next session to find a bag waiting on her bed, he knows what he's meant to do. He opens it with care, leaving most of the packaging intact.

The first thing out is a t-shirt, obviously cut to fit a girl. It's made of soft, pale blue jersey with some sort of curling abstract design in blue and silver, and Stiles immediately knows that it'll feel _amazing_ on. He puts it down gently and roots through the rest of the bag to find a dusky pink skirt made out of something that feels like a cross between corduroy and suede. It comes down to mid-thigh, and Stiles knows that it's something Lydia would choose for herself. Then there's a pair of jeans, medium wash, with some cute embroidery on the back pockets. Stiles spares a moment to be amazed at how _tiny_ the pockets in women's pants are - no wonder they always carry purses.

The shoes are black courts, patent leather, with a chunky heel of about an inch. Stiles would _love_ to know how she got these in his size. He'd also love to know how (and if) he's meant to walk in them, because he's clumsy enough in flat feet, but no doubt Lydia will have thought of that, because that's what she does.

And finally, right at the bottom of the bag, the underwear. He carefully pulls out a bra and panties which claim to be 'demi-cup' and 'bikini-cut' respectively, pale lilac with a bit of lace: ordinary-looking, not deliberately sexy lingerie or anything, which makes Stiles feel a bit better. He licks his lips nervously.

"What, no socks?" he asks weakly. Lydia, lounging in her computer chair, just smiles like a cat.

"Put them on," she says.

So he does. But first, he has to undress. In front of Lydia. He's done it before, but it never gets easier: he gets his shoes, socks and plaid overshirt off easily enough, but he always hesitates before taking off his t-shirt, then his pants, then finally his underwear to stand, naked and self-conscious, at the end of Lydia's bed, half-hard out of Pavlovian response because usually when Lydia gets him to strip for her it means that she's going to get him to finger himself so she can watch.

The panties feel very small when he picks them up, but when he steps into them (bending over in a way which he's sure sticks his ass out at Lydia) and slides them up his legs, they fit comfortably on his hips. They're not cut to accomodate male genitalia, and he spends a couple of minutes rearranging himself so the gusset doesn't dig uncomfortably into his balls. His half-hard cock makes an obvious bulge, and he hurries onto the bra in embarrassment.

It turns out that bra fastenings are not, in fact, as tricky as advertised - when you can see what you're doing. He tries several times to fasten it at the back before giving up and twisting it round to fasten it at the front, then twists it back round and pulls the straps up onto his shoulders. It's padded, but nothing can disguise how Stiles has nothing to put in the cups. There's no chicken fillets in the bag, so he assumes Lydia must want it this way.

"Turn around," says Lydia, and Stiles swallows and turns to face her. He knows he looks stupid dressed up like this in girl's underwear, with the gaping bra and the treasure trail, but Lydia's eyes are hot as she looks him up and down. His cock stiffens further, made obvious by the tight panties. He feels a flush working its way down his neck and chest. "Carry on," she says, approving, and Stiles gladly turns back to the rest of it.

The t-shirt is as soft as expected, and stretchy so that it manages to both fit his shoulders and cling to his waist, though it's a little loose at the hips. It also disguises the gap between his chest and the bra cups, giving Stiles a moment of cognitive dissonance when he looks down and finds that he now has at least a semi-convincing bust.

He pauses to consider the skirt and the jeans. He's pretty sure he's not meant to put _both_ of them on, but he can't work out which one Lydia wants.

"The jeans," says Lydia, reading his mind as usual. "We'll have to shave your legs for the skirt. Besides, I'm not convinced that those shoes would work with it." Stiles very carefully doesn't think about Lydia _shaving his legs, jesus_ , and instead pulls on the jeans. They're pretty tight, especially in the crotch, and the material's not as giving as the panties so his raging boner is super obvious. He bends down pick up the shoes slightly awkwardly - he's not used to pants being so tight around the thighs and ass, and he wriggles a bit before he realises that that's the point - but Lydia says, "No, changed my mind," so he leaves them and stands back up.

He turns around to face her, and he's not ready for what he finds. Lydia has slumped to hook each leg over the arms of her chair, spreading her thighs, and her fingers are busy inside her panties.

" _Fuck_ ," he says, shocked. He's seen her slide a hand up her skirt a few times in the heat of the moment, just to take the edge off, but never this - he's never seen her this obviously turned-on. He's never seen her come, never even seen her panties before. These ones are pale blue - and, he realises with a thrill, the exact same design as the ones she bought for him.

She must see in his face when he gets it, because she grins. Under the hot pulse of arousal, he wonders if her bra is the same as well.

"Get over here," she says, and Stiles nearly falls over his own feet - good job they didn't go with the heels after all - scrambling to stand in front of her. He knows not to touch.

"Pinch your tits," she says, and Stiles feels himself turn a dull red as he searches out his nipples through the layers of jersey and lace. He can't feel much through the padding, but the cups are pretty low so he gets his fingers into them without much fuss, though the top is still in the way, to get a better hold. He hasn't cut his nails in a while, and they're just long enough to add a bit of bite as he pinches and twists. They're not that sensitive, not really, but Lydia likes to watch him play with them and that turns him on just fine.

"Now you can touch your cock. Through the jeans," she adds, before Stiles can start on the zipper. He expected this, so he's not too disappointed - too busy cupping himself through the pants and sighing. He squeezes his fingers and rocks his hips into his hand a bit, letting his eyes close in relief. He can hear small, wet sounds and he immediately opens his eyes when he realises that they're coming from Lydia, whose fingers are working faster inside her panties.

"Oh _god_ , that's hot," he blurts, and Lydia laughs, a little breathless. He's about ninety percent sure that she's worked a finger inside herself, judging from the shape in the cotton, and he focusses desperately on the wallpaper pattern because if he thinks too hard about Lydia fingering herself he's going to come, and he knows Lydia won't want him to mess up these clothes. Yet.

It's two agonising minutes of heavy breathing and trying to hold off coming before Lydia says " _Now_ you can jerk off," and Stiles nearly sprains something opening the tight jeans, dragging them down to mid-thigh, along with the panties, and seizing his cock. His vision blurs as he pulls frantically at his dick, but he can still make out Lydia - fuck, is she grinding her clit against the heel of her hand? Her red mouth is open, though she's not making any sound - that's fine, Stiles is making enough noise for both of them. It used to embarrass him, but he realised pretty quickly that it turned Lydia on something fierce, so he got over it pretty quickly.

He stumbles forward as he comes, knees buckling to drop him to the carpet just in front of Lydia's chair, which results in him getting most of his come all over his hand and the floor and only a couple of drops on his jeans. He hopes this is acceptable to Lydia, because right now he hasn't the energy to apologise for making a mess. He looks up, still panting, and _wow_ , Lydia's really going for it. And he's got a first-row seat. She keeps jerking her hips, hand working furiously as she grinds herself towards orgasm, occasionally making little huffing sounds, speeding up until her breath suddenly catches and she switches to quick thrusts back and forth with a beat in between each, her face caught in what Stiles knows as her 'concentrating hard' expression. Fuck, that's her come face too. She's _coming_. He's never gonna be able to look at her in class again without popping a boner. _Awkward_. But this scene will be replayed in his jerk-off fantasies for the next three months _at least_ , so he commits it to memory.

Lydia is still gently moving her hips when she drops him the box of tissues. He cleans up as best he can and pulls up his pants, slightly distracted by the way her panties are moulded damply to her vulva. Wow. Okay. Stiles feels his dick twitch as he starts to get hard again, and, while he's usually pretty thrilled with his teenage lack of refractory period in these sessions, he's pretty sure that a) these jeans are gonna make it uncomfortable, and b) Lydia isn't gonna let him take care of it here.

He's right. She tells him to change and he does, carefully folding the girl's clothes and putting them back in the bag. He thinks Lydia will like that. She smirks a bit when she sees his hard-half cock through the panties - he hastily turns around, which is stupid because she's already seen his dick plenty but he's still self-conscious - but, as predicted, says nothing. It's nothing unusual: he thinks she likes knowing that when he gets home he'll jerk off to the memory.

She sends him out with a _I'll text you_. Cool and casual - but Stiles notices that she still hasn't taken her hand out of her panties.


End file.
